Thiatriphyrin(2.1.1): A Core-Modified Contracted Porphyrin

Elusive in its free‐base form, the core‐modified contracted porphyrin thiatriphyrin(2.1.1) was prepared with p‐tolyl substituents by intramolecular McMurry coupling and then converted into various alkoxy‐substituted analogues (see scheme; DBU=1,8‐diazabicyclo[5.4.0]undec‐7‐ene). In the presence of t...

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Published inAngewandte Chemie (International ed.) Vol. 52; no. 12; pp. 3360 - 3363
Main Authors Kuzuhara, Daiki, Sakakibara, Yuka, Mori, Shigeki, Okujima, Tetsuo, Uno, Hidemitsu, Yamada, Hiroko
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 18.03.2013
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Aromaticity
Chemistry
Chemistry, Multidisciplinary
core modification
Joining
Physical Sciences
porphyrinoids
Porphyrins
protonation
Science & Technology
triphyrins
porphyrinoids
ARYL-SUBSTITUTED SUBPORPHYRINS
protonation
VOLTAGE
core modification
SUBPHTHALOCYANINES
triphyrins
aromaticity
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Summary:Elusive in its free‐base form, the core‐modified contracted porphyrin thiatriphyrin(2.1.1) was prepared with p‐tolyl substituents by intramolecular McMurry coupling and then converted into various alkoxy‐substituted analogues (see scheme; DBU=1,8‐diazabicyclo[5.4.0]undec‐7‐ene). In the presence of trifluoroacetic acid (TFA), each of these compounds was transformed into the protonated thiatriphyrin(2.1.1), which exhibited moderate aromaticity.
Bibliography:ark:/67375/WNG-6P7ZTJR0-9
ArticleID:ANIE201209678
Ministry of Education, Culture, Sports, Science and Technology, MEXT (Japan)
istex:BED07B036C48E6F41DC5A8E3E803F41B9962C487
We thank S. Katao for the measurements of X-ray diffraction and M. Yamamura and Y. Nishikawa for ESIMS measurements. This research was partly supported by Grants-in-Aid (No. 24655034 to H.Y. and D.K.) and the Green Photonics Project at NAIST sponsored by the Ministry of Education, Culture, Sports, Science and Technology, MEXT (Japan).
We thank S. Katao for the measurements of X‐ray diffraction and M. Yamamura and Y. Nishikawa for ESIMS measurements. This research was partly supported by Grants‐in‐Aid (No. 24655034 to H.Y. and D.K.) and the Green Photonics Project at NAIST sponsored by the Ministry of Education, Culture, Sports, Science and Technology, MEXT (Japan).
KAKEN
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201209678